Crystal structure and packing energy calculations of (+)-6-aminopenicillanic acid.

IF 0.8 4区化学

Acta crystallographica. Section C, Crystal structure communications Pub Date : 2013-11-01 Epub Date: 2013-10-24 DOI:10.1107/S0108270113025924

Sofiane Saouane, Gernot Buth, Francesca P A Fabbiani

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引用次数: 3

Abstract

The X-ray single-crystal structure of (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, commonly known as (+)-6-aminopenicillanic acid (C8H12N2O3S) and a precursor of a variety of semi-synthetic penicillins, has been determined from synchrotron data at 150 K. The structure represents an ordered zwitterion and the crystals are nonmerohedrally twinned. The crystal structure is composed of a three-dimensional network built by three charge-assisted hydrogen bonds between the ammonium and carboxylate groups. The complementary analysis of the crystal packing by the PIXEL method brings to light the nature and ranking of the energetically most stabilizing intermolecular interaction energies. In accordance with the zwitterionic nature of the structure, PIXEL lattice energy calculations confirm the predominance of the Coulombic term (-379.1 kJ mol(-1)) ahead of the polarization (-141.4 kJ mol(-1)), dispersion (-133.7 kJ mol(-1)) and repulsion (266.3 kJ mol(-1)) contributions.

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(+)-6-氨基青霉素酸的晶体结构和包封能计算。

(2S,5R,6R)-6-氨基-3,3-二甲基-7-氧-4-硫-1-azabicyclo[3.2.0]庚烷-2-羧酸(俗称(+)-6-氨基青霉素酸(C8H12N2O3S)，是多种半合成青霉素的前体)的x射线单晶结构。结构为有序两性离子，晶体是非单面孪晶。晶体结构是由铵基和羧酸基之间的三个电荷辅助氢键组成的三维网络。利用PIXEL方法对晶体堆积进行互补分析，揭示了能量最稳定的分子间相互作用能的性质和排序。根据该结构的两性离子性质，PIXEL晶格能量计算证实了库仑项(-379.1 kJ mol(-1))在极化(-141.4 kJ mol(-1))、色散(-133.7 kJ mol(-1))和斥力(266.3 kJ mol(-1))贡献之前的优势。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Acta crystallographica. Section C, Crystal structure communications 化学-晶体学

自引率

12.50%

发文量

审稿时长

1 months

期刊介绍： Acta Crystallographica Section C: Structural Chemistry is continuing its transition to a journal that publishes exciting science with structural content, in particular, important results relating to the chemical sciences. Section C is the journal of choice for the rapid publication of articles that highlight interesting research facilitated by the determination, calculation or analysis of structures of any type, other than macromolecular structures. Articles that emphasize the science and the outcomes that were enabled by the study are particularly welcomed. Authors are encouraged to include mainstream science in their papers, thereby producing manuscripts that are substantial scientific well-rounded contributions that appeal to a broad community of readers and increase the profile of the authors.